Chemical changes of organic compounds in chlorinated water : XII. Gas chromatographic—mass spectrometric studies of the reactions of methylnaphthalenes with hypochlorite in dilute aqueous solution

Abstract

The products of aqueous chlorination reactions of naphthalene, 1- and 2-methylnaphthalenes, 1,2-, 1,3-, 1,4-, 1,5-, 1,8-, 2,3- and 2,6-dimethylnaphthalenes and 2,3,5-trimethylnaphthalene with hypochlorite have been determined by gas chromatography—mass spectrometry. They included chloro-substituted, oxygenated (quinones) and hydroxylated (phenols) compounds which were readily formed at room temperature. The extent of the reactions was shown to depend on the pH, the initial concentrations of both compounds and the number of methyl substituents and their positions. Monochlorinated compounds were identified in the chlorinated water under those conditions utilized for water treatment.